The objective of this proposal is to continue our studies on developing practical methods for the synthesis of novel bridged polycyclic compounds and biologically active alkaloids via intramolecular cycloaddition reactions of 1-acyldihydropyridines. Specific aims are (1) to complete the total synthesis of (plus/minus)-gephyrotoxin by the INOC or IMDA routes (2) to investigate approaches to the asymmetric synthesis of (+)- gephyrotoxin, and (3) to study an approach to the synthesis of the Lycopodium alkaloid, (+)-luciduline.